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922 N Pennsylvania Avenue

Winter Park, FL 32789
  • $1,995,000
  • STATUS: Active
  • ON SITE: 32 Days
  • MLS #: O6424685
UPDATED: 48 min ago
$1,995,000
  • 4
    BEDS
  • 0.17
    ACRES
  • 4
    BATHS
  • 0
    1/2 BATHS
  • 3,440
    SQFT
  • $580
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
2001
County:
Area:

School Information

Elementary School:
Middle School:
High School:

Description

Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.

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© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-08-15T23:43:24.437.
www.drummondrealty.net/homes/178806224
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922 N Pennsylvania Avenue Winter Park, FL 32789

  • Price: $1,995,000
  • Status: Active
  • On Site: 32 Days
  • Updated: 48 min ago
  • MLS #: O6424685
4
Beds
4
Baths
0
½ Baths
0.17
Acres
3,440
SQFT
$580
$/SQFT
2001
Built
Neighborhood:
Tantum Add
County:
Orange
Area:
Winter Park
Elementary School:
Lakemont Elem
Middle School:
Maitland Middle
High School:
Winter Park High
Property Description
Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.
Exterior Features

Architectural Style Mediterranean Attached Garage Yn Yes Carport Yn No Construction Materials BlockStucco Covered Spaces 2 Direction Faces North Exterior Features Awning(s)BalconyFrench DoorsIrrigation SystemLightingRain GuttersSidewalk Foundation Details Slab Lot Features City LotLandscapedLevel Lot Size Dimensions 100 x 75 Open Parking YN Yes Parking Features Circular Driveway Patio And Porch Features CoveredPatioRear PorchScreened Pool Private Yn No Road Frontage Type Street Paved Road Surface Type Paved Roof Tile View Golf Course Water Access Yn No Water Extras Yn No Water View Yn No Waterfront Yn No

Interior Features

Additional Rooms Den/Library/OfficeFormal Dining Room SeparateInside Utility Appliances Built-In OvenCooktopDishwasherDisposalDryerMicrowaveRefrigeratorTankless Water HeaterWasherWine Refrigerator Building Area Total 4288 Cooling Central AirZoned Cooling YN Yes Fireplace Features GasLiving Room Fireplace Yn Yes Flooring CarpetTileHardwood Furnished Unfurnished Heating CentralHeat PumpZoned Heating YN Yes Interior Features Built-in FeaturesCeiling Fan(s)Crown MoldingDry BarEating Space In KitchenHigh CeilingsLiving Room/Dining Room ComboPrimaryBedroom UpstairsSolid Wood CabinetsStone CountersWalk-In Closet(s)Window Treatments Laundry Features InsideLaundry Room Levels Two Rooms Living Room Kitchen (Kitchen Island) Dining Room Primary Bedroom 2 (En Suite BathroomWalk-In Closet(s)) Primary Bathroom (Split VanitiesTub with Separate Shower Stall) Office (Built-In ShelvingBuilt-in Features) Bedroom 3 (Built-in Closet) Bedroom 4 (Built-in Closet) Balcony/Porch/Lanai Dinette Foyer Primary Bedroom (En Suite BathroomWalk-In Closet(s)) Sewer Public Sewer Stories Total 2 Water Source Public

Property Features

Additional Lease Restrictions Please verify with City of Winter Park regarding any leasing restrictions. Additional Parcels YN No Association Yn No Cdd Yn No Down Payment Resource No Flood Zone Code X Garage Yn Yes Homestead Yn Yes Lease Considered YN Yes Lease Restrictions YN No Minimum Lease No Minimum New Construction Yn No Occupant Type Owner Ownership Fee Simple Pet Restrictions Please verify with City of Winter Park regarding any pet restrictions. Pets Allowed Yes Planned Unit Development Yn No Property Sub Type Single Family Residence Senior Community Yn No Special Listing Conditions None Tax Annual Amount 10684.15 Total Annual Fees 0 Total Monthly Fees 0 Utilities BB/HS Internet AvailablePropanePublicUnderground Utilities Zoning R-2


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of PREMIER SOTHEBY'S INTL. REALTY: 407-644-3295.



© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-08-15T23:43:24.437.
 
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